


Sweet As Candy

by purpleskiesandcherrypies



Category: Supernatural
Genre: Alternate Universe - High School, Coach Dean Winchester, Come Swallowing, Deepthroating, Dirty Talk, F/M, Oral Sex, POV Dean Winchester, Sex, Teasing
Language: English
Status: Completed
Published: 2018-07-10
Updated: 2018-07-10
Packaged: 2019-06-08 07:02:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,908
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15237975
Author URL: https://archiveofourown.org/users/purpleskiesandcherrypies/pseuds/purpleskiesandcherrypies
Summary: An AU where the Winchesters are brothers but not hunters. Sam ended up an successful but probably unhappy lawyer while Dean started his new job as a high school gym coach. Oh, and FYI, three of the cheerleaders are legal. What if one of them is a Lolita?





	Sweet As Candy

“Dude, this school is awesome. I think I’ve never had so much fun at a job!” Dean chirped into the phone.

“Maybe this time just make sure you’re going to keep that job of yours, Dean.” Sam said half-heartedly while his assistant held out a form for him to sign.

“Why do you think I can’t do that? Huh? You gotta have faith in your brother, Sam.” Dean sat down in his little office and played with a basketball. He sprawled his legs, letting them rest on the desk.

“Just, you know, I have a feeling that you’ll do something stupid?” Sam’s voice was more concern than warning.

“Me? Never.” Dean chuckled, acting like he doesn’t know what Sam means.

“One word, Dean. Jailbait.” Now, this time, it was a warning.

“I’ve been here a month, Sam. Nothing happened. And, oh, FYI, three of the cheerleaders are legal.” Dean joked but he knows that Sam isn’t laughing.

“Dean. I mean it!”

“Yeah, yeah. Whatever. But hey, I do have a big lawyer brother who could pull me out of this.” Dean winked but he realized that Sam doesn’t see him, nor is he really interested in his jokes. It wasn’t always like that. Sam was fun to be around, many years ago. Dean thinks that the corporate environment sucked him in, chewed on him and spit him out to stomp on him again. But it was what Sammy wanted and he’s here to support him. Well, lately Sam supported Dean. Help paying his bills when he was late and still searched for a job he could keep longer than a week.

“Alright, I’m due in court. See you on the weekend?” It was their thing, meeting at weekends. Some kind of a bonding thing their dad used to do when he was still alive. Fly fonding he used to call it. A mix between fly fishing and bonding while drinking beer and talk about what’s going on in their life. Sam and Dean had kept the tradition going.

“Sure thing. See ya, Sammy.” Just when Dean hung up, the bell rang. School was over. Dean’s packing his things to go home. He’ll probably spend his evening eating watered down ramen and later, he’d be sitting at a bar, flirting with the barmaid.

* * *

***

“Mr. Winchester?” The voice startled Dean as he looked up to see a student.

“Oh, Y/N?” He smiled a tired smile. “Did you knock? I didn’t hear it.” He leaned back on his chair lazily.

“Yeah. I’m sorry to disturb you.” She walked in, all slender and with a lollipop in her mouth. Dean could say it’s cherry. Her lips and tongue are deep red, he could see it as her tongue swirled around the candy.

She swayed her hips when she walked towards his desk and Dean felt his blood pumping down to his crotch.  _Damn it._

“I just wanted to inform you that we have a new routine for the next game.” She smiled before she put the candy into her mouth. She hollowed her cheeks and pulled it out with a pop.

Little Lolita is driving him crazy and Dean squirmed in his chair. He changed his position so as to not let her see his growing boner just by the sight of her sucking in that lollipop.

“Hhhm.” He cleared his throat. “Oh..o..Ok. Thanks for letting me know. I would need to see the routine before the game.” Dean’s mind was racing. He’s scanning his brain, trying to remember if she was one of the legal ones.

“Are you ok, coach?” She was standing before him now, sucking at that damn thing and looking down on him. She leaned against the desk, her ass half on it and it was firm. And round too.

“I’m ok. Thanks. So, do you have anything else you want to say? If not, I’d like to go home.” Dean would have to wait until she leaves because there’s no way he could stand up now. His hard dick was straining against the fabric of his sweats and now he’s really grateful for them, even if it sometimes makes him look like a stupid jock but the zip of his jeans would have left an imprint on his dick by now.

“Well, yeah.” She smiled that smile again and Dean thinks she just deliberately swirled her tongue around the round candy for him to see. “I hurt my ankle. Could you maybe take a look?”

She hopped on his desk and spread her legs before showing him her apparently hurt ankle.

“Oh.. uh.. Why don’t you go to see the nurse?” Dean tries not to look. It’s like a fucking accident. He knows he shouldn’t but also he can’t look away.

“I’ve been there, coach Winchester. Everyone already left.” She said it in a whiney voice while she leaned back and sucked away at her damn candy.

“Uh.. I’m afraid I can’t help you, Y/N.” Dean said, looking anywhere but directly a _t_  her or in between her legs.

“I have another pain, coach. Maybe you can help me with that?” She spread her legs even further apart.

_Jesus._

Dean tried to look away. Lord know he tried but her crotch was magnetic. It pulled his gaze  _right there_.

She hiked up the skirt of her uniform and she was bare. She didn’t even bother to wear her undergarments and that’s when Dean knows that hell probably has a special place for him. He knows that she’s legal but he also knows that he shouldn’t be doing what he’s doing now.

God, he can’t help it. Not when she’s looking at him like this. Not when she pulled out the lollipop with a pop from her lips and put it  _right there_.

“It hurts here, coach.” She grinned as she rubbed the still wet candy on her bare cunt, drawing circles on her bud while she spread her folds with the other hand, leaving red cherry streaks  _right there_.

Dean couldn’t say a word. He opened up his mouth to say something. Maybe tell her to stop and go home. But he couldn’t. He was mesmerized looking at the wet trails of the cherry candy. Little red patches that drops down on his desk.

“Maybe you could kiss the pain away, Mr. Winchester?”

“I-I.. uh.. I’m afraid I can’t do that, Y/N.” He said it but he really didn’t mean it. He wants nothing more than kissing her pain away but he also knows that he would like to keep his job.

“Mr. Winchester. You know you want to.” She trailed off, taking the candy into her mouth again and sucked at it deliciously.

Dean let out a groan and his mouth starts to water at the sight.

“You’re 18, right?” He swallowed his saliva down before looking at her and she nodded her head, a smirk on her face.

With that, the little will power Dean was holding on to, was gone. He threw it over board and he only hoped that Sam will forgive him.

He took the lollipop from her hand and rub it against her clit. “Does this make you feel better?”

“Uh huh..” She looked down at him and nodded frantically before spreading her legs more and placed them on each side of his shoulder.

He draws circles and watch the slick cherry flavored wetness running down, pooling at his desk before he put it back to her mouth for her to suck it, making it wet again before he continued his game. He could do that for hours but he also really,  _really_  wants to taste her.

He drenched the lollipop in her wetness again and this time? This time he put it to his mouth and sucked it in, drawing a moan from her when she watched him. Dean gave her the candy back and she put it in her mouth, filling the left side of her cheek with it and he wished that it was his dick that was making her cheek bulge.

“Please, coach? Kiss the pain away? It hurts so,  _so_  bad.” She moved her hips, to and fro, inviting him to taste her and Dean didn’t need to be asked twice. Not anymore. He can’t let this opportunity slip and he will probably lose his job but he has no self-control and he knows it. Sam will probably suggest therapy, like he’s a fucking basket case.

He lowered his head to her pussy and flattened his tongue against her bare cunt to take a lick. She yelps at the feeling before she began to relax and enjoy it. He let the tip of his tongue swirl around her bud while he parted her folds with one hand. The other one went up to her mouth, thumb brushing against her soft lips and then she took out her candy and sucked at his thumb instead.

_Fucking Lolita._

She swirled her tongue around the head of his thumb, sucking at it like it was some delicious lollipop and he did the same to her cunt, coaxing moans from her and making her tongue vibrate against his thumb.

He took his finger out of her mouth but was met with restraint, followed by a sigh of disappointment. He looked up at her and chuckled lightly.

Dean massages along her entrance, probing the hole with his middle finger before he slid it in and it went in,  _just like that_.

She gasps for air when she felt him stretching her and damn she was tight. He worked his finger in and out, stretching her a bit before he could even  _think_ about adding another finger. She looked at him with a beautiful agony and when he finally being able to add another finger, she lost it. She threw her head back before looking down at him again and biting down on her bottom lip.

He began to lick her bud, humming a beautiful melody while his fingers worked their way inside of her and curving themselves up to give her pleasure.

“Shit. You look so good eating me out, coach.” She said through gritted teeth and it made him look up at her, holding her gaze while he sucked and scissored her.

“Ah shit. Fuck. Coach!” She clasps her knees around his head, and caged him in while she came, pushing her cunt to his face and rode out her orgasm, smearing her sweet juice everywhere on his face.

When she came down from her heights she started to giggle. That little innocent giggle that makes Dean want to shut her up. Maybe he will. No, he’s  _sure_  he would.

Dean took his time, lapping at her cunt, slurping up every last drop before he came up again. He sucked at his fingers and brushed away the remains on his face with the back of his hand before he got up from his chair.

“Now tell me, would you like to suck on another lollipop?” He said it with a grin and was met with her bright smile in return.

With one swift motion, his pants and boxers were down and his dick sprung free, hitting his stomach and Dean watched her eyes grow wide. The boys her age weren’t that impressive, he could tell.

She turned herself around and lay flat on his desk while she licked her lips and it was the perfect height for him. He stepped closer and he could feel his dick twitching, chasing her mouth, when her breath hits the tip.

_Fuck, he doesn’t know if he’ll get out of here alive._

She planted a soft kiss on the tip and it sends shudder through his body.

_Calm down, Dean! You’ve got this._

And then he felt her tongue swirling around the tip, spreading pre cum around it and Dean threw his head back and closed his eyes.

_Fuck, not yet, Dean. Not yet._

And  _just like that_ , without so much of a warning, she pushed herself forward and took him in, her nose hitting his stomach as he tickled the back of her throat with the tip of his dick, feeling the tightness of her throat closing in on him.

“Fuck, sweetheart. You’re a fucking pro!” He was surprised, to say the least.

Dean places his hand on her head, gripping at the sides behind her ears and held her head still. “Open up for me, baby girl.” He cooed and she did. She looked up at him with her tears strained eyes and there was a spark of glee. Dean could tell.

He then held her head still while he worked his hips, pushing himself into her and stilled when he reached the end. Like that. Over and over. When he pulled out again, a string of thick saliva was attached to his dick and she took it, rubbing it on his shaft and sucked at the tip, all this, while grinning at him. Dean’s heart felt full as she couldn’t stop looking at her with awe in his eyes.

“Please fuck me, coach.” She purred against his dick and yes, Dean isn’t going to deny her that.

He made her lie on her back, as his hands tugged at her legs, pulling her to the edge of the desk. She propped herself up on her elbows as Dean draped one of her leg over his shoulder. She’s fucking bendy and Dean wonders why he never dated a cheerleader in school.

She watched as he positioned his cock at her entrance and stroke it along her folds, slicking it up with sticky sweet juice before he pushed his tip in. Slowly, he pushed himself further, huffing and puffing profanities as his dick enters her tight canal.

“You haven’t been fucked that much, honey?” He asked her, as his thumb start to draw little circles on her clit, making her gasps for air as it felt so fucking good.

“Not as much as I would want to, Mr. Winchester.” She bit down on her bottom lip as she felt him sliding in, filling her up to the hilt. “Shit, you’re so big, coach!” She panted and if this comment didn’t make his heart swell with pride.

Dean thrusted into her agonizingly slow but he had to, if he didn’t want to blow it right now. His other hand went up to push up her top, revealing her bare tits. Naughty little girl came here with a plan and he smiled to himself, as his fingers pinched at her hard nipples, making her yelp up in pleasure.

“Mmh.. Mr. Winchester. You like fucking my pussy, huh?” She said seductively and oh god, he almost came upon hearing her dirty talk.

“Fuck. You’re a star, Y/N.” He panted and picked up his pace. “I wanna make you cum. Cum for me, sweetheart. Can you do that, huh? Squeeze down on my big cock?”

He circled his thumb on her clit in the same pace as his thrust. It wasn’t long until he felt her legs quiver, giving in to the pressure of her orgasm and then he felt her inner walls clamping down on him, keeping him in place so that there was neither a way in, nor a way out.

Dean had to wait while her pussy pulsed around his cock and he was sure that he’s going to burst at any given moment.

“Where do you want me to cum, kitten?” His voice a low groan and he had to concentrate not to fill her up.

She didn’t answer but she pushed herself away from him and Dean felt the cold air hitting his cock, making him sigh. He wanted to stay in there but certainly Lolita here had some other ideas.

She smiled as she knelt down in front of him and he felt both her hands stroking his cock up and down, while she licked and sucked at the tip. She looked up at him with anticipation and shit, Dean couldn’t hold back no more. He closed his eyes shortly but then he forced himself to look at her again. He’d kick himself in the ass if he would miss that picture of her. That moment when the strings of cum came shooting out of him and onto her face.

She had some of it on her cheek and nose. The rest, she licked up and sucked softly at his tip, making sure to milk him dry.

Dean chuckled when he pulled her up again. He licked at her cheeks and her nose, cleaning her of his cum before he kissed her and pushed the cum into her mouth, making her swallow it all.

“Thank you, Mr Winchester.” She placed a soft kiss on his lips before she tucked her clothes into place.

“Uh.. you’re welcome. And don’t forget to show me the new routine.” He said while he pulled his boxers and pants up again and sat back down in his chair.

“Oh, we will.” She winked before she skipped to the door. “And Mr. Winchester?”

Dean looked up from his desk. “Yes?”

“I don’t think the pain will go away so soon. Will you maybe help me out again tomorrow?”

“Oh? Yes, yes. Why not.” He acted cool not showing her that on the inside, his heart skipped a beat.

“Thanks.” She blew him a kiss before she closed the door behind her.


End file.
